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The structures of bis­[(R)-(+)-1-phenyl­ethyl­ammonium] (2R,3R)-(−)-2,3-di-p-toluoyloxybutane­dioate methanol disolvate monohydrate, 2C8H12N+·C20H16O82−·2CH4O·H2O, (I), and bis­(benzyl­ammonium) (2R,3R)-(−)-2,3-di-p-toluoyl­oxy­butane­­dioate dihydrate, 2C7H10N+·C20H16O82−·2H2O, (II), exhibit extensive hydrogen bonding, with (N—)H...O and (O—)H...O distances in the ranges 2.716 (2)–2.929 (3) and 2.687 (2)–2.767 (2) Å, respectively, in (I), and 2.673 (2)–2.888 (2) and 2.785 (2)–2.931 (2) Å, respectively, in (II). The amine groups are protonated and the carboxyl­ate groups of the tartrate anions are fully deprotonated. The conformation of the toluoyltartrate anion and its mol­ecular parameters are similar in both structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106015149/gg1300sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106015149/gg1300Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106015149/gg1300IIsup3.hkl
Contains datablock II

CCDC references: 612466; 612467

Comment top

This work arose from a systematic study of chiral host acids with amine guests. Previous examples of the structures derived from the host (2R,3R)-(-)-di-O-p-toluoyltartaric acid or its enantiomer with amines showed that the acid is mono-deprotonated (Liao et al. 2003; Hansen et al. 1998). Liao et al. (2003) have characterized the structure of (R)-α-{[(1,1-dimethylethyl)ammonio]methyl}-(3,5-dihydroxyphenyl)methanol (2S,3S)-di-O-toluoyltartrate monohydrate, in which the N atom on the base is protonated and one of the carboxylic acid moieties is deprotonated. The anhydrous salt of the same compound has similar features [Cambridge Structural Database (CSD; Allen, 2002), reference codes GACXUE and GACYEP01, respectively]. Hansen et al. (1998) have described the structure of (+)-(R)-3-(N,N-dimethylammonio)-1,1-diphenyl-1-butanol (-)-(2R,3R)-O,O'-di-p-toloyltartrate, in which the base is again protonated on the N atom and one carboxylic acid moiety is anionic (CSD reference code GORCAR). In contrast, the structure of (2S,5S)-1,6-diammonio-2,5-dimethyl-3,4-dithiahexane (2S,3S)-di-O-(4-toluoyl)tartrate ethanol solvate sesquihydrate (Elz et al., 1987) shows the thiahexane to be bis-protonated and the tartrate to have lost two H atoms (CSD reference code FEWLEY). We noted these features by observing the C—O bond lengths of the carboxylic acid moieties in which there was no ambiguity as to whether the carboxylic acid moiety was deprotonated or not. In addition, the corresponding amines displayed an extra H atom at N, the geometry of which was tetrahedral. We have also analysed differences in the conformations of the tartrate anions and have noted that the absolute value of the torsion angle about the central C—C bond is approximately 76° in the completely deprotonated anion, but is reduced to 61–70° in the monoprotonated species. There were no discernible patterns in the other four torsion angles in the adjacent C—O and O—C bonds of the tartrates, which are described later.

We have characterized the structures of (2R,3R)-toluoyltartaric acid, L, with (R)-(+)-1-phenylethylamine (A) and benzylamine (B) (see scheme), and present the results here. The former forms a compound with the stoichiometry L.2A·2MeOH·H2O [compound (I); Fig. 1] and the latter a compound with the stoichiometry L.2B·2H2O [compound (II); Fig. 2].

Compound (I) crystallizes in the space group P21 with Z = 2. The refinement showed that the N atoms of the amines are protonated and the carboxyl moieties of the acid exhibit similar C—O bond lengths, ranging from 1.240 (3) to 1.257 (3) Å, so they may be represented as (CO2) moieties.

The structure is extensively hydrogen-bonded, as shown in Fig. 3. There are double ribbons of the toluoyltartrate anions running in the [010] direction, which are bridged by 1-phenylethylammonium cations and water molecules, while the methanol molecules are hydrogen bonded to the amine and the acid ions. Details of the hydrogen bonding are given in Table 2.

The conformation of the toluoyltartrate anion is governed by the torsion angles about the central C—C bond and the adjacent C—O and O—C bonds. These are reported in Table 1, together with salient bond lengths. The conformation is such that the aromatic toluoyl moieties lie approximately perpendicular to each other.

Compound (II) crystallizes in the space group P212121 with Z = 4. The toluoyltartaric acid again forms anions, with both its carboxyl moieties deprotonated, and the amines display protonated N atoms. The packing is such that the structure forms infinite sheets perpendicular to [001] and is held together by hydrogen bonds, in which the water molecules and amine cations bridge the acid anions. This is shown in Fig. 4. Details of the hydrogen bonding are given in Table 4. The conformation of the toluoyltartrate in this structure is similar to that of (I), as are the C—O bond lengths of the anionic carboxyl moiety (Table 3).

We note that the absolute values of the torsion angles about the central C—C bond of the anions in these compounds are close to that found in the dithiahexane compound elucidated by Elz et al. (1987).

Experimental top

Tartaric acid and the appropriate amine guest, in a mole ratio of 1:2, were dissolved in warm wet methanol solvent (Temperature? Ratio of alcohol and water?). The resultant solutions were allowed to stand at room temperature. Colourless crystals of (I) and (II) appeared after a few days from their respective mother liquor.

Refinement top

Both structure solutions and refinements proceeded routinely. Friedel equivalents were merged in the final refinement cycles. All non-H atoms were refined anisotropically. The functional H atoms of the methanol hydroxyl group, the water hydroxyl group and the amine cation NH3+ were located in a difference electron-density map and refined independently with simple bond-length constraints (Restraints?). [Please give details of restraints used and ranges of refined distances.] The remaining H atoms were placed in idealized positions in a riding model, with C—H = 0.95–1.00 Å, and refined with Uiso(H) = 1.2–1.5Ueq(C).

Computing details top

For both compounds, data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), X-SEED (Barbour, 2001) and POVRAY (Cason, Year?); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. All H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A view of the asymmetric unit of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. All H atoms have been omitted for clarity.
[Figure 3] Fig. 3. A projection of the structure of (I), viewed along [100], showing the network of hydrogen bonding. Various shading is used for different molecules and bonds, and hydrogen bonds are shown as dotted lines. All H atoms have been omitted for clarity.
[Figure 4] Fig. 4. A perspective view of (II), along [100], showing the infinite sheets of the hydrogen-bonding network running perpendicular to [001]. Hydrogen bonds are shown as dotted lines. All H atoms have been omitted for clarity.
(I) bis[(R)-(+)-1-phenylethylammonium] (2R,3R)-(-)-2,3-di-p-toluoyloxybutanedioate methanol disolvate monohydrate top
Crystal data top
2C8H12N+·C20H16O82·2CH4O·H2OF(000) = 760
Mr = 710.80Dx = 1.242 Mg m3
Monoclinic, P21Melting point: not measured K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 10.9366 (1) ÅCell parameters from 43385 reflections
b = 8.0785 (1) Åθ = 3.8–26.4°
c = 22.0995 (2) ŵ = 0.09 mm1
β = 103.324 (1)°T = 113 K
V = 1899.96 (3) Å3Prism, colourless
Z = 20.40 × 0.40 × 0.35 mm
Data collection top
Nonius Kappa CCD area-detector
diffractometer
3969 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.009
Graphite monochromatorθmax = 26.4°, θmin = 4.2°
1.2° ϕ scans and ω scansh = 1313
7708 measured reflectionsk = 1010
7708 independent reflectionsl = 2727
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0488P)2 + 0.6269P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
7708 reflectionsΔρmax = 0.38 e Å3
502 parametersΔρmin = 0.26 e Å3
11 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.035 (3)
Crystal data top
2C8H12N+·C20H16O82·2CH4O·H2OV = 1899.96 (3) Å3
Mr = 710.80Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.9366 (1) ŵ = 0.09 mm1
b = 8.0785 (1) ÅT = 113 K
c = 22.0995 (2) Å0.40 × 0.40 × 0.35 mm
β = 103.324 (1)°
Data collection top
Nonius Kappa CCD area-detector
diffractometer
3969 reflections with I > 2σ(I)
7708 measured reflectionsRint = 0.009
7708 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03611 restraints
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.38 e Å3
7708 reflectionsΔρmin = 0.26 e Å3
502 parameters
Special details top

Experimental. Half sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 35 mm; combination of ϕ and ω scans of 1.2°, 40 s per °, 2 iterations.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.43263 (16)0.6310 (2)0.33632 (8)0.0251 (4)
O20.49430 (15)0.7944 (2)0.41991 (7)0.0232 (3)
O30.57209 (15)1.2349 (2)0.28196 (7)0.0231 (3)
O40.64452 (14)1.0498 (2)0.22387 (7)0.0222 (3)
O50.40860 (13)0.8900 (2)0.25667 (6)0.0188 (3)
O60.22347 (14)0.9170 (2)0.28353 (7)0.0258 (4)
O70.67107 (13)0.81505 (19)0.31307 (7)0.0182 (3)
O80.84887 (14)0.9665 (2)0.33804 (8)0.0239 (4)
O410.8126 (2)1.0909 (3)0.14869 (12)0.0573 (7)
O510.62194 (16)0.7457 (2)0.16569 (8)0.0304 (4)*
O610.44125 (19)0.3114 (2)0.37065 (9)0.0322 (4)
N210.42734 (19)0.1116 (3)0.46770 (9)0.0235 (4)
N310.48447 (18)0.5304 (3)0.22150 (9)0.0226 (4)
C10.4638 (2)0.7666 (3)0.36273 (10)0.0187 (4)
C20.47025 (19)0.9173 (3)0.32111 (9)0.0177 (4)
H20.42911.01340.33700.021*
C30.60531 (19)0.9638 (3)0.32204 (10)0.0175 (4)
H30.64521.01220.36350.021*
C40.60896 (18)1.0931 (3)0.27086 (10)0.0180 (4)
C50.28199 (19)0.9076 (3)0.24356 (10)0.0200 (4)
C60.2279 (2)0.9206 (3)0.17572 (10)0.0226 (5)
C70.3012 (2)0.9489 (3)0.13326 (11)0.0267 (5)
H70.39020.95170.14690.032*
C80.2453 (2)0.9732 (4)0.07107 (12)0.0338 (6)
H80.29630.99270.04230.041*
C90.1150 (3)0.9694 (4)0.05017 (12)0.0382 (6)
C100.0428 (2)0.9387 (4)0.09291 (13)0.0405 (7)
H100.04610.93370.07910.049*
C110.0971 (2)0.9153 (4)0.15494 (12)0.0325 (6)
H110.04590.89570.18360.039*
C120.0539 (3)1.0028 (6)0.01719 (14)0.0586 (10)
H12C0.00300.91150.03380.088*
H12B0.11891.01220.04100.088*
H12A0.00621.10640.02050.088*
C130.79791 (19)0.8364 (3)0.32204 (10)0.0183 (4)
C140.8628 (2)0.6832 (3)0.31045 (10)0.0183 (4)
C150.9850 (2)0.6969 (3)0.30298 (11)0.0231 (5)
H151.02200.80310.30230.028*
C161.0530 (2)0.5564 (3)0.29654 (12)0.0267 (5)
H161.13710.56720.29220.032*
C171.0006 (2)0.3997 (3)0.29625 (11)0.0256 (5)
C180.8757 (2)0.3874 (3)0.30105 (12)0.0271 (5)
H180.83700.28160.29900.033*
C190.8078 (2)0.5269 (3)0.30871 (11)0.0225 (5)
H190.72360.51640.31280.027*
C201.0744 (3)0.2453 (4)0.29061 (14)0.0344 (6)
H20C1.06600.21890.24660.052*
H20A1.04200.15310.31110.052*
H20B1.16310.26350.31050.052*
C210.2857 (2)0.1047 (3)0.44991 (11)0.0267 (5)
H210.25970.09280.40370.032*
C220.2375 (2)0.0442 (3)0.47825 (11)0.0272 (5)
C230.1547 (4)0.1501 (6)0.44080 (15)0.0765 (15)
H230.13070.12970.39730.092*
C240.1055 (4)0.2862 (6)0.46522 (18)0.0852 (17)
H240.04830.35760.43850.102*
C250.1391 (3)0.3182 (4)0.52799 (13)0.0415 (7)
H250.10440.40980.54520.050*
C260.2244 (3)0.2145 (4)0.56548 (12)0.0371 (6)
H260.25090.23740.60870.045*
C270.2720 (3)0.0779 (4)0.54123 (11)0.0343 (6)
H270.32890.00640.56800.041*
C280.2339 (3)0.2681 (4)0.46704 (14)0.0374 (6)
H28A0.14220.26860.45230.056*
H28C0.26970.35930.44750.056*
H28B0.25620.28180.51230.056*
C310.3672 (2)0.5026 (3)0.17225 (11)0.0265 (5)
H310.32310.61120.16270.032*
C320.3971 (2)0.4375 (3)0.11329 (10)0.0239 (5)
C330.3242 (3)0.4885 (4)0.05607 (12)0.0346 (6)
H330.25960.56810.05460.042*
C340.3454 (3)0.4238 (4)0.00136 (12)0.0425 (7)
H340.29400.45730.03750.051*
C350.4403 (3)0.3116 (5)0.00291 (12)0.0444 (8)
H350.45630.26990.03470.053*
C360.5126 (3)0.2595 (5)0.05951 (13)0.0439 (7)
H360.57780.18110.06070.053*
C370.4904 (2)0.3210 (4)0.11455 (11)0.0325 (6)
H370.53940.28300.15330.039*
C380.2818 (3)0.3860 (4)0.19759 (14)0.0409 (7)
H38A0.20210.37300.16680.061*
H38C0.26550.43200.23600.061*
H38B0.32270.27780.20630.061*
C410.8471 (3)1.2483 (5)0.13378 (18)0.0555 (9)
H41C0.84561.32400.16820.083*
H41A0.78801.28720.09620.083*
H41B0.93201.24490.12640.083*
C510.7326 (3)0.6892 (4)0.14846 (12)0.0356 (6)
H51C0.78000.78450.13860.053*
H51A0.70910.61740.11190.053*
H51B0.78470.62690.18300.053*
H21B0.461 (3)0.009 (2)0.4576 (14)0.036 (8)*
H61B0.434 (4)0.4279 (14)0.3695 (19)0.067 (12)*
H31B0.541 (2)0.601 (3)0.2058 (13)0.039 (8)*
H21A0.454 (3)0.179 (4)0.4372 (13)0.051 (10)*
H410.756 (3)1.107 (7)0.1776 (16)0.085 (15)*
H21C0.454 (2)0.141 (4)0.5107 (6)0.029 (7)*
H31A0.524 (3)0.427 (2)0.2353 (14)0.041 (8)*
H510.650 (3)0.843 (3)0.1925 (15)0.063 (11)*
H31C0.464 (3)0.582 (4)0.2564 (10)0.037 (8)*
H61A0.489 (3)0.277 (6)0.3425 (15)0.072 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0381 (9)0.0137 (8)0.0272 (8)0.0002 (7)0.0150 (7)0.0000 (6)
O20.0302 (8)0.0195 (8)0.0219 (7)0.0014 (7)0.0100 (6)0.0027 (7)
O30.0298 (8)0.0141 (8)0.0274 (8)0.0030 (7)0.0105 (6)0.0026 (6)
O40.0258 (7)0.0197 (8)0.0236 (7)0.0015 (7)0.0111 (6)0.0019 (7)
O50.0185 (7)0.0174 (8)0.0215 (7)0.0028 (6)0.0064 (6)0.0018 (6)
O60.0214 (7)0.0265 (9)0.0319 (8)0.0005 (7)0.0109 (6)0.0011 (7)
O70.0179 (7)0.0139 (7)0.0236 (7)0.0030 (6)0.0063 (6)0.0011 (6)
O80.0212 (7)0.0183 (8)0.0317 (8)0.0004 (6)0.0052 (6)0.0029 (7)
O410.0675 (15)0.0475 (14)0.0702 (16)0.0074 (12)0.0432 (13)0.0048 (12)
O610.0466 (10)0.0172 (9)0.0405 (10)0.0039 (8)0.0262 (8)0.0051 (8)
N210.0318 (10)0.0188 (9)0.0214 (9)0.0010 (9)0.0088 (8)0.0004 (8)
N310.0310 (10)0.0155 (9)0.0228 (9)0.0020 (8)0.0095 (7)0.0001 (8)
C10.0206 (10)0.0131 (10)0.0260 (11)0.0035 (8)0.0125 (8)0.0024 (8)
C20.0200 (10)0.0146 (10)0.0196 (9)0.0019 (8)0.0068 (8)0.0001 (8)
C30.0198 (9)0.0121 (10)0.0215 (10)0.0022 (8)0.0068 (8)0.0003 (8)
C40.0154 (9)0.0164 (10)0.0222 (10)0.0006 (8)0.0040 (8)0.0017 (8)
C50.0192 (9)0.0116 (10)0.0303 (11)0.0006 (8)0.0083 (8)0.0004 (9)
C60.0223 (10)0.0158 (11)0.0289 (11)0.0020 (9)0.0040 (8)0.0004 (9)
C70.0245 (10)0.0242 (12)0.0309 (11)0.0004 (10)0.0053 (9)0.0012 (10)
C80.0326 (12)0.0379 (15)0.0308 (12)0.0009 (11)0.0069 (10)0.0058 (11)
C90.0372 (13)0.0422 (16)0.0313 (13)0.0065 (12)0.0001 (11)0.0010 (12)
C100.0238 (11)0.0530 (19)0.0410 (14)0.0045 (13)0.0002 (10)0.0049 (14)
C110.0228 (11)0.0379 (15)0.0362 (13)0.0011 (11)0.0055 (9)0.0025 (12)
C120.0496 (17)0.085 (3)0.0347 (15)0.0104 (19)0.0046 (13)0.0061 (18)
C130.0185 (9)0.0180 (11)0.0185 (9)0.0019 (9)0.0044 (8)0.0021 (8)
C140.0192 (10)0.0179 (11)0.0178 (9)0.0027 (9)0.0041 (8)0.0011 (8)
C150.0222 (10)0.0204 (11)0.0273 (11)0.0019 (9)0.0072 (9)0.0019 (9)
C160.0192 (10)0.0269 (13)0.0371 (12)0.0003 (10)0.0126 (9)0.0031 (10)
C170.0259 (11)0.0218 (12)0.0313 (12)0.0041 (10)0.0112 (9)0.0015 (10)
C180.0288 (12)0.0152 (11)0.0402 (13)0.0007 (9)0.0138 (10)0.0027 (10)
C190.0186 (10)0.0198 (11)0.0303 (11)0.0000 (9)0.0084 (8)0.0023 (10)
C200.0319 (13)0.0253 (13)0.0494 (16)0.0066 (11)0.0162 (11)0.0008 (12)
C210.0281 (11)0.0268 (12)0.0243 (11)0.0001 (10)0.0042 (9)0.0036 (10)
C220.0297 (11)0.0272 (13)0.0245 (11)0.0014 (10)0.0060 (9)0.0044 (10)
C230.104 (3)0.079 (3)0.0295 (15)0.058 (3)0.0200 (17)0.0237 (17)
C240.098 (3)0.087 (3)0.050 (2)0.065 (3)0.027 (2)0.030 (2)
C250.0457 (15)0.0374 (16)0.0430 (15)0.0041 (13)0.0133 (12)0.0163 (13)
C260.0597 (17)0.0288 (14)0.0255 (12)0.0056 (13)0.0153 (11)0.0050 (11)
C270.0525 (15)0.0274 (13)0.0217 (11)0.0005 (12)0.0060 (10)0.0007 (10)
C280.0367 (14)0.0302 (15)0.0467 (15)0.0085 (12)0.0122 (12)0.0071 (12)
C310.0277 (11)0.0192 (12)0.0322 (12)0.0047 (10)0.0061 (9)0.0010 (10)
C320.0259 (11)0.0204 (12)0.0253 (10)0.0034 (9)0.0054 (8)0.0011 (9)
C330.0342 (12)0.0300 (14)0.0344 (13)0.0034 (11)0.0029 (10)0.0058 (11)
C340.0489 (16)0.0490 (18)0.0238 (12)0.0172 (15)0.0038 (11)0.0078 (13)
C350.0481 (16)0.063 (2)0.0244 (12)0.0205 (16)0.0121 (11)0.0118 (14)
C360.0384 (14)0.057 (2)0.0367 (14)0.0056 (14)0.0096 (11)0.0159 (14)
C370.0356 (12)0.0362 (15)0.0236 (11)0.0081 (12)0.0027 (9)0.0032 (11)
C380.0367 (14)0.0472 (17)0.0448 (15)0.0086 (13)0.0218 (12)0.0116 (14)
C410.0544 (19)0.049 (2)0.066 (2)0.0035 (17)0.0207 (16)0.0036 (18)
C510.0417 (14)0.0385 (15)0.0286 (12)0.0071 (13)0.0121 (11)0.0028 (12)
Geometric parameters (Å, º) top
O1—C11.251 (3)C16—H160.9500
O2—C11.251 (3)C17—C181.398 (3)
O3—C41.257 (3)C17—C201.506 (3)
O4—C41.240 (3)C18—C191.381 (3)
O5—C21.445 (2)C18—H180.9500
O7—C31.437 (2)C19—H190.9500
C1—C21.537 (3)C20—H20C0.9800
C2—C31.520 (3)C20—H20A0.9800
C3—C41.547 (3)C20—H20B0.9800
O7—C131.366 (2)C21—C221.507 (4)
O6—C51.207 (3)C21—C281.519 (4)
O5—C51.355 (2)C21—H211.0000
O8—C131.204 (3)C22—C231.375 (4)
O41—C411.387 (5)C22—C271.383 (3)
O41—H411.00 (4)C23—C241.387 (5)
O51—C511.425 (3)C23—H230.9500
O51—H510.99 (3)C24—C251.375 (5)
O61—H61B0.944 (12)C24—H240.9500
O61—H61A0.94 (3)C25—C261.379 (4)
N21—C211.509 (3)C25—H250.9500
N21—H21B0.95 (3)C26—C271.379 (4)
N21—H21A0.96 (3)C26—H260.9500
N21—H21C0.959 (10)C27—H270.9500
N31—C311.495 (3)C28—H28A0.9800
N31—H31B0.958 (10)C28—H28C0.9800
N31—H31A0.953 (10)C28—H28B0.9800
N31—H31C0.95 (3)C31—C321.509 (3)
C2—H21.0000C31—C381.522 (4)
C3—H31.0000C31—H311.0000
C5—C61.483 (3)C32—C371.383 (3)
C6—C71.386 (3)C32—C331.393 (3)
C6—C111.399 (3)C33—C341.385 (4)
C7—C81.384 (3)C33—H330.9500
C7—H70.9500C34—C351.372 (5)
C8—C91.393 (4)C34—H340.9500
C8—H80.9500C35—C361.382 (4)
C9—C101.387 (4)C35—H350.9500
C9—C121.509 (4)C36—C371.386 (4)
C10—C111.376 (4)C36—H360.9500
C10—H100.9500C37—H370.9500
C11—H110.9500C38—H38A0.9800
C12—H12C0.9800C38—H38C0.9800
C12—H12B0.9800C38—H38B0.9800
C12—H12A0.9800C41—H41C0.9800
C13—C141.478 (3)C41—H41A0.9800
C14—C151.388 (3)C41—H41B0.9800
C14—C191.395 (3)C51—H51C0.9800
C15—C161.383 (3)C51—H51A0.9800
C15—H150.9500C51—H51B0.9800
C16—C171.389 (4)
C5—O5—C2114.60 (15)C18—C19—H19120.0
C13—O7—C3113.48 (16)C14—C19—H19120.0
C41—O41—H41106 (3)C17—C20—H20C109.5
C51—O51—H51105 (2)C17—C20—H20A109.5
H61B—O61—H61A109 (4)H20C—C20—H20A109.5
C21—N21—H21B109.9 (19)C17—C20—H20B109.5
C21—N21—H21A107 (2)H20C—C20—H20B109.5
H21B—N21—H21A97 (3)H20A—C20—H20B109.5
C21—N21—H21C108.9 (16)C22—C21—N21111.0 (2)
H21B—N21—H21C114 (3)C22—C21—C28113.8 (2)
H21A—N21—H21C119 (3)N21—C21—C28108.8 (2)
C31—N31—H31B109.9 (18)C22—C21—H21107.7
C31—N31—H31A110 (2)N21—C21—H21107.7
H31B—N31—H31A111 (3)C28—C21—H21107.7
C31—N31—H31C109.7 (18)C23—C22—C27118.2 (3)
H31B—N31—H31C109 (3)C23—C22—C21119.5 (2)
H31A—N31—H31C107 (3)C27—C22—C21122.4 (2)
O2—C1—O1127.5 (2)C22—C23—C24121.3 (3)
O2—C1—C2115.11 (19)C22—C23—H23119.3
O1—C1—C2117.36 (18)C24—C23—H23119.3
O5—C2—C3106.40 (16)C25—C24—C23120.2 (3)
O5—C2—C1113.17 (18)C25—C24—H24119.9
C3—C2—C1111.48 (17)C23—C24—H24119.9
O5—C2—H2108.6C24—C25—C26118.6 (3)
C3—C2—H2108.6C24—C25—H25120.7
C1—C2—H2108.6C26—C25—H25120.7
O7—C3—C2107.91 (17)C27—C26—C25121.0 (2)
O7—C3—C4111.45 (16)C27—C26—H26119.5
C2—C3—C4110.22 (16)C25—C26—H26119.5
O7—C3—H3109.1C26—C27—C22120.6 (3)
C2—C3—H3109.1C26—C27—H27119.7
C4—C3—H3109.1C22—C27—H27119.7
O4—C4—O3126.6 (2)C21—C28—H28A109.5
O4—C4—C3119.19 (19)C21—C28—H28C109.5
O3—C4—C3114.16 (18)H28A—C28—H28C109.5
O6—C5—O5122.56 (19)C21—C28—H28B109.5
O6—C5—C6125.49 (19)H28A—C28—H28B109.5
O5—C5—C6111.91 (17)H28C—C28—H28B109.5
C7—C6—C11119.3 (2)N31—C31—C32111.13 (18)
C7—C6—C5122.5 (2)N31—C31—C38108.8 (2)
C11—C6—C5118.0 (2)C32—C31—C38112.1 (2)
C8—C7—C6120.2 (2)N31—C31—H31108.3
C8—C7—H7119.9C32—C31—H31108.3
C6—C7—H7119.9C38—C31—H31108.3
C7—C8—C9120.7 (2)C37—C32—C33119.0 (2)
C7—C8—H8119.7C37—C32—C31121.7 (2)
C9—C8—H8119.7C33—C32—C31119.2 (2)
C10—C9—C8118.6 (2)C34—C33—C32120.3 (3)
C10—C9—C12120.8 (3)C34—C33—H33119.8
C8—C9—C12120.6 (3)C32—C33—H33119.8
C11—C10—C9121.3 (2)C35—C34—C33120.4 (2)
C11—C10—H10119.3C35—C34—H34119.8
C9—C10—H10119.3C33—C34—H34119.8
C10—C11—C6119.8 (2)C34—C35—C36119.7 (3)
C10—C11—H11120.1C34—C35—H35120.2
C6—C11—H11120.1C36—C35—H35120.2
C9—C12—H12C109.5C35—C36—C37120.4 (3)
C9—C12—H12B109.5C35—C36—H36119.8
H12C—C12—H12B109.5C37—C36—H36119.8
C9—C12—H12A109.5C32—C37—C36120.2 (2)
H12C—C12—H12A109.5C32—C37—H37119.9
H12B—C12—H12A109.5C36—C37—H37119.9
O8—C13—O7122.57 (19)C31—C38—H38A109.5
O8—C13—C14124.99 (19)C31—C38—H38C109.5
O7—C13—C14112.43 (18)H38A—C38—H38C109.5
C15—C14—C19119.3 (2)C31—C38—H38B109.5
C15—C14—C13117.9 (2)H38A—C38—H38B109.5
C19—C14—C13122.76 (18)H38C—C38—H38B109.5
C16—C15—C14120.1 (2)O41—C41—H41C109.5
C16—C15—H15119.9O41—C41—H41A109.5
C14—C15—H15119.9H41C—C41—H41A109.5
C15—C16—C17121.16 (19)O41—C41—H41B109.5
C15—C16—H16119.4H41C—C41—H41B109.5
C17—C16—H16119.4H41A—C41—H41B109.5
C16—C17—C18118.3 (2)O51—C51—H51C109.5
C16—C17—C20121.8 (2)O51—C51—H51A109.5
C18—C17—C20119.9 (2)H51C—C51—H51A109.5
C19—C18—C17120.9 (2)O51—C51—H51B109.5
C19—C18—H18119.6H51C—C51—H51B109.5
C17—C18—H18119.6H51A—C51—H51B109.5
C18—C19—C14120.10 (19)
C5—O5—C2—C3156.8 (2)O8—C13—C14—C19162.0 (2)
C5—O5—C2—C180.5 (2)O7—C13—C14—C1917.5 (3)
O2—C1—C2—O5167.05 (17)C19—C14—C15—C162.7 (3)
O1—C1—C2—O514.9 (3)C13—C14—C15—C16175.3 (2)
O2—C1—C2—C373.1 (2)C14—C15—C16—C171.2 (4)
O1—C1—C2—C3105.0 (2)C15—C16—C17—C181.6 (4)
C13—O7—C3—C2171.0 (2)C15—C16—C17—C20178.7 (3)
C13—O7—C3—C467.9 (2)C16—C17—C18—C192.9 (4)
O5—C2—C3—O776.3 (2)C20—C17—C18—C19177.4 (2)
C1—C2—C3—O747.5 (2)C17—C18—C19—C141.4 (4)
O5—C2—C3—C445.6 (2)C15—C14—C19—C181.5 (3)
C1—C2—C3—C4169.39 (17)C13—C14—C19—C18176.5 (2)
O7—C3—C4—O412.6 (3)N21—C21—C22—C23127.8 (3)
C2—C3—C4—O4107.2 (2)C28—C21—C22—C23109.1 (4)
O7—C3—C4—O3168.47 (17)N21—C21—C22—C2753.2 (3)
C2—C3—C4—O371.7 (2)C28—C21—C22—C2769.9 (3)
C2—O5—C5—O612.1 (3)C27—C22—C23—C240.7 (7)
C2—O5—C5—C6165.5 (2)C21—C22—C23—C24178.3 (4)
O6—C5—C6—C7164.0 (2)C22—C23—C24—C250.1 (8)
O5—C5—C6—C713.6 (3)C23—C24—C25—C261.4 (7)
O6—C5—C6—C1111.4 (4)C24—C25—C26—C272.3 (5)
O5—C5—C6—C11171.0 (2)C25—C26—C27—C221.7 (4)
C11—C6—C7—C80.6 (4)C23—C22—C27—C260.2 (5)
C5—C6—C7—C8174.8 (2)C21—C22—C27—C26179.2 (2)
C6—C7—C8—C90.1 (4)N31—C31—C32—C3740.2 (3)
C7—C8—C9—C100.8 (5)C38—C31—C32—C3781.7 (3)
C7—C8—C9—C12177.5 (3)N31—C31—C32—C33143.7 (2)
C8—C9—C10—C111.2 (5)C38—C31—C32—C3394.4 (3)
C12—C9—C10—C11177.1 (3)C37—C32—C33—C340.3 (4)
C9—C10—C11—C60.7 (5)C31—C32—C33—C34176.5 (2)
C7—C6—C11—C100.2 (4)C32—C33—C34—C351.5 (4)
C5—C6—C11—C10175.4 (3)C33—C34—C35—C361.9 (5)
C3—O7—C13—O82.5 (3)C34—C35—C36—C370.5 (5)
C3—O7—C13—C14178.0 (2)C33—C32—C37—C361.6 (4)
O8—C13—C14—C1516.0 (3)C31—C32—C37—C36177.8 (3)
O7—C13—C14—C15164.54 (19)C35—C36—C37—C321.2 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21A···O610.95 (3)1.80 (2)2.716 (3)158 (3)
N21—H21B···O2i0.96 (1)1.99 (1)2.929 (3)166 (3)
N21—H21C···O2ii0.95 (1)1.95 (2)2.846 (3)155 (3)
N31—H31A···O3i0.95 (3)1.87 (1)2.795 (3)162 (3)
N31—H31B···O510.96 (1)1.82 (1)2.768 (3)170 (3)
N31—H31C···O10.95 (3)1.92 (1)2.843 (2)165 (3)
O41—H41···O41.00 (4)1.82 (2)2.767 (3)158 (5)
O51—H51···O40.99 (3)1.82 (2)2.757 (3)158 (3)
O61—H61A···O3i0.94 (3)1.81 (3)2.750 (2)172 (4)
O61—H61B···O10.94 (1)1.80 (2)2.687 (2)156 (4)
Symmetry codes: (i) x, y1, z; (ii) x+1, y1/2, z+1.
(II) Bis(benylammonium) (2R,3R)-(-)-2,3-di-p-toluoyloxybutanedioate dihydrate top
Crystal data top
2C7H10N+·C20H16O82·2H2ODx = 1.249 Mg m3
Mr = 636.68Melting point: not measured K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 28526 reflections
a = 6.8805 (1) Åθ = 4.3–27.2°
b = 19.2606 (1) ŵ = 0.09 mm1
c = 25.5545 (2) ÅT = 113 K
V = 3386.55 (6) Å3Prism, colourless
Z = 40.35 × 0.25 × 0.25 mm
F(000) = 1352
Data collection top
Nonius Kappa CCD area-detector
diffractometer
3955 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 27.2°, θmin = 4.3°
1.2° ϕ scans and ω scansh = 88
28533 measured reflectionsk = 2424
4225 independent reflectionsl = 3232
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084 w = 1/[σ2(Fo2) + (0.048P)2 + 0.6428P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
4225 reflectionsΔρmax = 0.28 e Å3
458 parametersΔρmin = 0.26 e Å3
10 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.017 (2)
Crystal data top
2C7H10N+·C20H16O82·2H2OV = 3386.55 (6) Å3
Mr = 636.68Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 6.8805 (1) ŵ = 0.09 mm1
b = 19.2606 (1) ÅT = 113 K
c = 25.5545 (2) Å0.35 × 0.25 × 0.25 mm
Data collection top
Nonius Kappa CCD area-detector
diffractometer
3955 reflections with I > 2σ(I)
28533 measured reflectionsRint = 0.027
4225 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.03410 restraints
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.28 e Å3
4225 reflectionsΔρmin = 0.26 e Å3
458 parameters
Special details top

Experimental. Half sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 36 mm; combination of ϕ and ω scans of 1.2°, 60 s per °, 2 iterations.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.33566 (17)0.03978 (6)0.28175 (5)0.0244 (3)
O20.64601 (18)0.03542 (6)0.25560 (5)0.0253 (3)
O30.26410 (17)0.28670 (6)0.24921 (5)0.0230 (3)
O40.57696 (18)0.29712 (6)0.27143 (5)0.0251 (3)
O50.62623 (17)0.16345 (5)0.21189 (4)0.0205 (2)
O60.51992 (19)0.10642 (6)0.14061 (5)0.0295 (3)
O70.55520 (16)0.17262 (5)0.32548 (4)0.0195 (2)
O80.3413 (2)0.21682 (10)0.38221 (6)0.0542 (5)
O410.1472 (2)0.41262 (6)0.20589 (6)0.0307 (3)
O510.98173 (18)0.10972 (6)0.28272 (5)0.0290 (3)
N210.7301 (2)0.40433 (7)0.20404 (6)0.0266 (3)
N310.9297 (2)0.25097 (7)0.30575 (6)0.0247 (3)
C10.4861 (2)0.06404 (8)0.26049 (6)0.0196 (3)
C20.4579 (2)0.13857 (7)0.23949 (6)0.0187 (3)
H20.34430.13890.21510.022*
C30.4158 (2)0.18741 (7)0.28461 (6)0.0181 (3)
H30.28280.17690.29830.022*
C40.4212 (2)0.26425 (8)0.26732 (6)0.0185 (3)
C50.6402 (3)0.14244 (8)0.16165 (6)0.0215 (3)
C60.8176 (3)0.16925 (8)0.13568 (6)0.0221 (3)
C70.9560 (3)0.20864 (8)0.16180 (7)0.0256 (3)
H70.93790.21990.19770.031*
C81.1202 (3)0.23148 (10)0.13565 (7)0.0298 (4)
H81.21370.25870.15380.036*
C91.1503 (3)0.21518 (9)0.08327 (7)0.0294 (4)
C101.0125 (3)0.17495 (10)0.05773 (7)0.0301 (4)
H101.03210.16290.02210.036*
C110.8476 (3)0.15219 (9)0.08319 (7)0.0274 (4)
H110.75450.12490.06500.033*
C121.3301 (3)0.24014 (13)0.05544 (8)0.0447 (5)
H12A1.31750.23110.01790.067*
H12C1.44390.21550.06910.067*
H12B1.34590.29010.06130.067*
C130.4907 (3)0.18590 (9)0.37432 (7)0.0269 (4)
C140.6260 (3)0.16301 (9)0.41548 (7)0.0257 (4)
C150.7930 (3)0.12479 (9)0.40495 (7)0.0290 (4)
H150.81760.10860.37050.035*
C160.9229 (3)0.11047 (10)0.44471 (8)0.0388 (5)
H161.03770.08490.43720.047*
C170.8877 (4)0.13302 (11)0.49569 (8)0.0430 (5)
C180.7170 (4)0.16865 (12)0.50588 (8)0.0443 (5)
H180.68860.18260.54070.053*
C190.5884 (3)0.18407 (11)0.46668 (7)0.0363 (4)
H190.47320.20920.47440.044*
C201.0316 (5)0.11925 (15)0.53895 (10)0.0644 (8)
H20C1.00480.07380.55460.097*
H20B1.01990.15540.56570.097*
H20A1.16370.11960.52460.097*
C210.6365 (3)0.36911 (9)0.15866 (8)0.0343 (4)
H21D0.49570.36440.16580.041*
H21E0.69130.32180.15530.041*
C220.6627 (4)0.40659 (9)0.10768 (8)0.0358 (5)
C230.5155 (5)0.44949 (11)0.08932 (10)0.0578 (7)
H230.40280.45650.11010.069*
C240.5300 (8)0.48183 (14)0.04171 (12)0.0810 (12)
H240.42870.51140.02990.097*
C250.6880 (8)0.47153 (16)0.01180 (12)0.0855 (13)
H250.69540.49290.02160.103*
C260.8398 (6)0.4304 (2)0.02885 (12)0.0846 (12)
H260.95220.42460.00770.102*
C270.8269 (5)0.39682 (15)0.07807 (10)0.0578 (7)
H270.92960.36820.09030.069*
C310.9356 (3)0.28543 (8)0.35819 (7)0.0275 (4)
H31E1.05030.26870.37790.033*
H31D0.81770.27280.37830.033*
C320.9460 (3)0.36328 (8)0.35255 (6)0.0244 (3)
C331.1244 (3)0.39668 (11)0.35171 (9)0.0385 (5)
H331.24120.37070.35460.046*
C341.1310 (4)0.46842 (13)0.34660 (10)0.0531 (7)
H341.25290.49160.34620.064*
C350.9626 (5)0.50598 (10)0.34212 (9)0.0534 (7)
H350.96870.55500.33840.064*
C360.7850 (4)0.47338 (10)0.34293 (8)0.0408 (5)
H360.66870.49970.34010.049*
C370.7766 (3)0.40159 (9)0.34785 (7)0.0278 (4)
H370.65420.37870.34800.033*
H21A0.8687 (15)0.4048 (13)0.2000 (9)0.041 (6)*
H31A1.031 (3)0.2643 (12)0.2826 (7)0.039 (6)*
H41A0.201 (4)0.3767 (10)0.2261 (9)0.054 (7)*
H21B0.691 (3)0.3812 (10)0.2352 (6)0.030 (5)*
H31B0.942 (4)0.2020 (5)0.3098 (9)0.043 (6)*
H41B0.211 (5)0.4508 (12)0.2210 (12)0.079 (10)*
H51B0.877 (3)0.0874 (12)0.2666 (9)0.049 (7)*
H21C0.695 (4)0.4519 (6)0.2091 (9)0.043 (6)*
H31C0.809 (2)0.2630 (11)0.2897 (8)0.030 (5)*
H51A1.091 (3)0.0805 (11)0.2825 (10)0.052 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0205 (6)0.0160 (5)0.0368 (6)0.0019 (5)0.0028 (5)0.0024 (5)
O20.0200 (6)0.0175 (5)0.0384 (7)0.0032 (5)0.0007 (5)0.0010 (5)
O30.0188 (6)0.0181 (5)0.0320 (6)0.0009 (5)0.0034 (5)0.0019 (5)
O40.0206 (6)0.0163 (5)0.0385 (6)0.0018 (5)0.0011 (5)0.0020 (5)
O50.0190 (6)0.0191 (5)0.0234 (5)0.0023 (4)0.0028 (5)0.0013 (4)
O60.0287 (7)0.0297 (6)0.0300 (6)0.0062 (6)0.0001 (5)0.0045 (5)
O70.0172 (5)0.0189 (5)0.0223 (5)0.0007 (5)0.0002 (5)0.0004 (4)
O80.0374 (9)0.0924 (13)0.0326 (7)0.0332 (10)0.0003 (7)0.0118 (8)
O410.0301 (7)0.0214 (6)0.0406 (7)0.0019 (5)0.0048 (6)0.0022 (5)
O510.0186 (6)0.0218 (6)0.0465 (7)0.0011 (5)0.0016 (6)0.0076 (5)
N210.0298 (8)0.0163 (6)0.0338 (8)0.0031 (6)0.0044 (7)0.0007 (6)
N310.0167 (6)0.0184 (6)0.0388 (8)0.0001 (6)0.0006 (6)0.0014 (6)
C10.0201 (8)0.0151 (6)0.0237 (7)0.0007 (6)0.0024 (6)0.0025 (6)
C20.0158 (7)0.0164 (6)0.0240 (7)0.0011 (6)0.0001 (6)0.0004 (6)
C30.0148 (7)0.0163 (7)0.0233 (7)0.0001 (6)0.0013 (6)0.0006 (6)
C40.0175 (7)0.0155 (7)0.0224 (7)0.0007 (6)0.0018 (6)0.0020 (6)
C50.0237 (8)0.0159 (6)0.0248 (7)0.0024 (7)0.0000 (7)0.0005 (6)
C60.0233 (8)0.0182 (7)0.0247 (8)0.0042 (7)0.0023 (7)0.0011 (6)
C70.0277 (9)0.0247 (8)0.0245 (8)0.0011 (7)0.0032 (7)0.0005 (6)
C80.0278 (9)0.0306 (8)0.0311 (9)0.0050 (8)0.0020 (7)0.0009 (7)
C90.0267 (9)0.0316 (9)0.0300 (9)0.0038 (8)0.0050 (8)0.0096 (7)
C100.0324 (10)0.0363 (9)0.0216 (8)0.0074 (8)0.0031 (7)0.0037 (7)
C110.0281 (9)0.0301 (8)0.0241 (8)0.0019 (8)0.0009 (7)0.0014 (7)
C120.0374 (11)0.0604 (13)0.0362 (10)0.0079 (11)0.0107 (10)0.0103 (10)
C130.0263 (9)0.0292 (8)0.0253 (8)0.0026 (7)0.0025 (7)0.0019 (7)
C140.0272 (9)0.0249 (8)0.0250 (8)0.0006 (7)0.0000 (7)0.0027 (6)
C150.0347 (10)0.0267 (8)0.0256 (8)0.0047 (8)0.0014 (8)0.0021 (7)
C160.0429 (11)0.0368 (10)0.0366 (10)0.0117 (10)0.0065 (10)0.0013 (8)
C170.0553 (14)0.0408 (10)0.0329 (10)0.0075 (11)0.0150 (10)0.0003 (8)
C180.0579 (14)0.0494 (12)0.0256 (9)0.0107 (12)0.0035 (10)0.0036 (9)
C190.0400 (11)0.0410 (10)0.0278 (9)0.0056 (9)0.0022 (8)0.0006 (8)
C200.078 (2)0.0713 (17)0.0435 (12)0.0238 (17)0.0290 (14)0.0080 (12)
C210.0395 (11)0.0227 (8)0.0408 (10)0.0046 (8)0.0030 (9)0.0025 (7)
C220.0484 (12)0.0221 (8)0.0367 (10)0.0063 (9)0.0015 (9)0.0061 (7)
C230.086 (2)0.0360 (11)0.0519 (13)0.0122 (13)0.0125 (14)0.0040 (10)
C240.147 (4)0.0446 (13)0.0520 (15)0.005 (2)0.024 (2)0.0001 (12)
C250.162 (4)0.0501 (15)0.0443 (15)0.038 (2)0.018 (2)0.0026 (12)
C260.104 (3)0.094 (2)0.0558 (16)0.048 (2)0.0332 (19)0.0228 (17)
C270.0596 (16)0.0585 (14)0.0551 (14)0.0141 (14)0.0160 (13)0.0103 (12)
C310.0266 (8)0.0223 (7)0.0336 (9)0.0012 (7)0.0004 (8)0.0015 (7)
C320.0258 (9)0.0212 (7)0.0262 (8)0.0020 (7)0.0029 (7)0.0014 (6)
C330.0331 (10)0.0378 (10)0.0444 (11)0.0105 (9)0.0048 (9)0.0035 (9)
C340.0651 (17)0.0436 (12)0.0506 (13)0.0343 (13)0.0000 (12)0.0039 (11)
C350.094 (2)0.0211 (9)0.0453 (11)0.0136 (12)0.0155 (14)0.0052 (8)
C360.0649 (15)0.0232 (9)0.0344 (10)0.0109 (10)0.0106 (10)0.0038 (8)
C370.0311 (9)0.0240 (8)0.0283 (9)0.0022 (7)0.0020 (8)0.0030 (7)
Geometric parameters (Å, º) top
O1—C11.259 (2)C14—C151.391 (3)
O2—C11.237 (2)C14—C191.394 (2)
O3—C41.253 (2)C15—C161.381 (3)
O4—C41.249 (2)C15—H150.9500
O5—C21.438 (2)C16—C171.394 (3)
O7—C31.446 (2)C16—H160.9500
C1—C21.545 (2)C17—C181.385 (3)
C2—C31.516 (2)C17—C201.508 (3)
C3—C41.545 (2)C18—C191.369 (3)
O5—C51.350 (2)C18—H180.9500
O6—C51.206 (2)C19—H190.9500
O7—C131.349 (2)C20—H20C0.9800
O8—C131.205 (2)C20—H20B0.9800
O41—H41A0.939 (10)C20—H20A0.9800
O41—H41B0.94 (3)C21—C221.500 (3)
O51—H51B0.937 (10)C21—H21D0.9900
O51—H51A0.937 (10)C21—H21E0.9900
N21—C211.490 (2)C22—C271.373 (4)
N21—H21A0.959 (10)C22—C231.389 (4)
N21—H21B0.951 (10)C23—C241.371 (4)
N21—H21C0.956 (10)C23—H230.9500
N31—C311.496 (2)C24—C251.343 (6)
N31—H31A0.949 (10)C24—H240.9500
N31—H31B0.952 (10)C25—C261.382 (6)
N31—H31C0.955 (10)C25—H250.9500
C2—H21.0000C26—C271.417 (4)
C3—H31.0000C26—H260.9500
C5—C61.482 (2)C27—H270.9500
C6—C71.388 (2)C31—C321.508 (2)
C6—C111.397 (2)C31—H31E0.9900
C7—C81.385 (3)C31—H31D0.9900
C7—H70.9500C32—C371.385 (3)
C8—C91.391 (3)C32—C331.385 (3)
C8—H80.9500C33—C341.389 (3)
C9—C101.388 (3)C33—H330.9500
C9—C121.505 (3)C34—C351.371 (4)
C10—C111.379 (3)C34—H340.9500
C10—H100.9500C35—C361.374 (4)
C11—H110.9500C35—H350.9500
C12—H12A0.9800C36—C371.390 (3)
C12—H12C0.9800C36—H360.9500
C12—H12B0.9800C37—H370.9500
C13—C141.472 (3)
C5—O5—C2115.08 (12)C16—C15—H15120.1
C13—O7—C3114.37 (13)C14—C15—H15120.1
H41A—O41—H41B100 (2)C15—C16—C17120.8 (2)
H51B—O51—H51A110 (2)C15—C16—H16119.6
C21—N21—H21A110.4 (15)C17—C16—H16119.6
C21—N21—H21B108.4 (13)C18—C17—C16118.51 (19)
H21A—N21—H21B112 (2)C18—C17—C20120.4 (2)
C21—N21—H21C115.6 (15)C16—C17—C20121.1 (2)
H21A—N21—H21C105 (2)C19—C18—C17121.18 (19)
H21B—N21—H21C105 (2)C19—C18—H18119.4
C31—N31—H31A114.7 (14)C17—C18—H18119.4
C31—N31—H31B109.9 (14)C18—C19—C14120.2 (2)
H31A—N31—H31B106 (2)C18—C19—H19119.9
C31—N31—H31C107.5 (13)C14—C19—H19119.9
H31A—N31—H31C107.7 (17)C17—C20—H20C109.5
H31B—N31—H31C111 (2)C17—C20—H20B109.5
O2—C1—O1127.56 (14)H20C—C20—H20B109.5
O2—C1—C2119.40 (14)C17—C20—H20A109.5
O1—C1—C2113.04 (14)H20C—C20—H20A109.5
O5—C2—C3108.66 (12)H20B—C20—H20A109.5
O5—C2—C1112.25 (13)N21—C21—C22113.89 (15)
C3—C2—C1109.66 (12)N21—C21—H21D108.8
O5—C2—H2108.7C22—C21—H21D108.8
C3—C2—H2108.7N21—C21—H21E108.8
C1—C2—H2108.7C22—C21—H21E108.8
O7—C3—C2107.49 (12)H21D—C21—H21E107.7
O7—C3—C4112.29 (12)C27—C22—C23119.7 (2)
C2—C3—C4111.86 (12)C27—C22—C21120.8 (2)
O7—C3—H3108.4C23—C22—C21119.5 (2)
C2—C3—H3108.4C24—C23—C22121.1 (3)
C4—C3—H3108.4C24—C23—H23119.4
O4—C4—O3126.61 (13)C22—C23—H23119.4
O4—C4—C3118.82 (14)C25—C24—C23119.8 (4)
O3—C4—C3114.56 (13)C25—C24—H24120.1
O6—C5—O5123.22 (16)C23—C24—H24120.1
O6—C5—C6124.45 (15)C24—C25—C26121.1 (3)
O5—C5—C6112.33 (14)C24—C25—H25119.4
C7—C6—C11119.25 (16)C26—C25—H25119.4
C7—C6—C5122.69 (15)C25—C26—C27119.6 (3)
C11—C6—C5118.04 (16)C25—C26—H26120.2
C8—C7—C6120.10 (16)C27—C26—H26120.2
C8—C7—H7119.9C22—C27—C26118.6 (3)
C6—C7—H7119.9C22—C27—H27120.7
C7—C8—C9120.96 (18)C26—C27—H27120.7
C7—C8—H8119.5N31—C31—C32110.89 (14)
C9—C8—H8119.5N31—C31—H31E109.5
C10—C9—C8118.49 (17)C32—C31—H31E109.5
C10—C9—C12121.16 (17)N31—C31—H31D109.5
C8—C9—C12120.34 (18)C32—C31—H31D109.5
C11—C10—C9121.18 (16)H31E—C31—H31D108.0
C11—C10—H10119.4C37—C32—C33119.79 (15)
C9—C10—H10119.4C37—C32—C31119.85 (17)
C10—C11—C6120.01 (17)C33—C32—C31120.36 (18)
C10—C11—H11120.0C32—C33—C34119.5 (2)
C6—C11—H11120.0C32—C33—H33120.2
C9—C12—H12A109.5C34—C33—H33120.2
C9—C12—H12C109.5C35—C34—C33120.3 (2)
H12A—C12—H12C109.5C35—C34—H34119.8
C9—C12—H12B109.5C33—C34—H34119.8
H12A—C12—H12B109.5C34—C35—C36120.61 (17)
H12C—C12—H12B109.5C34—C35—H35119.7
O8—C13—O7121.95 (17)C36—C35—H35119.7
O8—C13—C14124.61 (17)C35—C36—C37119.6 (2)
O7—C13—C14113.33 (15)C35—C36—H36120.2
C15—C14—C19119.28 (17)C37—C36—H36120.2
C15—C14—C13122.87 (16)C32—C37—C36120.2 (2)
C19—C14—C13117.77 (17)C32—C37—H37119.9
C16—C15—C14119.86 (17)C36—C37—H37119.9
C5—O5—C2—C3156.6 (1)O8—C13—C14—C15177.1 (2)
C5—O5—C2—C181.94 (15)O7—C13—C14—C156.6 (2)
O2—C1—C2—O55.00 (19)O8—C13—C14—C196.3 (3)
O1—C1—C2—O5175.61 (13)O7—C13—C14—C19169.93 (16)
O2—C1—C2—C3115.88 (16)C19—C14—C15—C162.5 (3)
O1—C1—C2—C363.51 (17)C13—C14—C15—C16174.04 (19)
C13—O7—C3—C2151.0 (1)C14—C15—C16—C170.9 (3)
C13—O7—C3—C485.53 (16)C15—C16—C17—C181.6 (3)
O5—C2—C3—O776.5 (1)C15—C16—C17—C20178.3 (2)
C1—C2—C3—O746.49 (16)C16—C17—C18—C192.6 (3)
O5—C2—C3—C447.17 (17)C20—C17—C18—C19177.3 (2)
C1—C2—C3—C4170.19 (13)C17—C18—C19—C141.0 (3)
O7—C3—C4—O428.5 (2)C15—C14—C19—C181.5 (3)
C2—C3—C4—O492.48 (17)C13—C14—C19—C18175.2 (2)
O7—C3—C4—O3152.91 (13)N21—C21—C22—C2784.8 (2)
C2—C3—C4—O386.13 (17)N21—C21—C22—C2397.8 (2)
C2—O5—C5—O61.2 (2)C27—C22—C23—C240.7 (4)
C2—O5—C5—C6179.4 (1)C21—C22—C23—C24176.7 (2)
O6—C5—C6—C7177.72 (16)C22—C23—C24—C250.7 (4)
O5—C5—C6—C72.9 (2)C23—C24—C25—C262.0 (5)
O6—C5—C6—C110.4 (2)C24—C25—C26—C271.8 (5)
O5—C5—C6—C11178.94 (14)C23—C22—C27—C260.9 (3)
C11—C6—C7—C81.0 (2)C21—C22—C27—C26176.5 (2)
C5—C6—C7—C8179.11 (16)C25—C26—C27—C220.3 (4)
C6—C7—C8—C90.4 (3)N31—C31—C32—C3787.1 (2)
C7—C8—C9—C100.5 (3)N31—C31—C32—C3392.5 (2)
C7—C8—C9—C12179.74 (18)C37—C32—C33—C340.5 (3)
C8—C9—C10—C110.9 (3)C31—C32—C33—C34179.86 (19)
C12—C9—C10—C11179.87 (18)C32—C33—C34—C350.3 (4)
C9—C10—C11—C60.4 (3)C33—C34—C35—C360.4 (4)
C7—C6—C11—C100.6 (3)C34—C35—C36—C370.6 (3)
C5—C6—C11—C10178.81 (15)C33—C32—C37—C360.8 (3)
C3—O7—C13—O810.3 (2)C31—C32—C37—C36179.64 (17)
C3—O7—C13—C14173.4 (1)C35—C36—C37—C320.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21A···O41i0.96 (1)1.93 (1)2.875 (2)169 (2)
N21—H21B···O40.95 (1)2.02 (1)2.888 (2)150 (2)
N21—H21C···O1ii0.96 (1)1.72 (1)2.673 (2)172 (2)
N31—H31A···O3i0.95 (1)1.87 (1)2.803 (2)168 (2)
N31—H31B···O510.95 (1)1.93 (1)2.807 (2)153 (2)
N31—H31C···O40.96 (1)1.79 (1)2.729 (2)168 (2)
O41—H41A···O30.94 (1)1.88 (1)2.785 (2)160 (2)
O41—H41B···O2ii0.94 (3)2.00 (3)2.931 (2)173 (3)
O51—H51A···O1i0.94 (1)1.86 (1)2.783 (2)168 (2)
O51—H51B···O20.94 (1)1.90 (1)2.804 (2)162 (2)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1/2, z+1/2.

Experimental details

(I)(II)
Crystal data
Chemical formula2C8H12N+·C20H16O82·2CH4O·H2O2C7H10N+·C20H16O82·2H2O
Mr710.80636.68
Crystal system, space groupMonoclinic, P21Orthorhombic, P212121
Temperature (K)113113
a, b, c (Å)10.9366 (1), 8.0785 (1), 22.0995 (2)6.8805 (1), 19.2606 (1), 25.5545 (2)
α, β, γ (°)90, 103.324 (1), 9090, 90, 90
V3)1899.96 (3)3386.55 (6)
Z24
Radiation typeMo KαMo Kα
µ (mm1)0.090.09
Crystal size (mm)0.40 × 0.40 × 0.350.35 × 0.25 × 0.25
Data collection
DiffractometerNonius Kappa CCD area-detector
diffractometer
Nonius Kappa CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7708, 7708, 3969 28533, 4225, 3955
Rint0.0090.027
(sin θ/λ)max1)0.6260.643
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.095, 1.12 0.034, 0.084, 1.07
No. of reflections77084225
No. of parameters502458
No. of restraints1110
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.38, 0.260.28, 0.26

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), X-SEED (Barbour, 2001) and POVRAY (Cason, Year?), SHELXL97.

Selected geometric parameters (Å, º) for (I) top
O1—C11.251 (3)O7—C31.437 (2)
O2—C11.251 (3)C1—C21.537 (3)
O3—C41.257 (3)C2—C31.520 (3)
O4—C41.240 (3)C3—C41.547 (3)
O5—C21.445 (2)
C5—O5—C2—C3156.8 (2)C2—O5—C5—C6165.5 (2)
C13—O7—C3—C2171.0 (2)C3—O7—C13—C14178.0 (2)
O5—C2—C3—O776.3 (2)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N21—H21A···O610.95 (3)1.80 (2)2.716 (3)158 (3)
N21—H21B···O2i0.96 (1)1.99 (1)2.929 (3)166 (3)
N21—H21C···O2ii0.95 (1)1.95 (2)2.846 (3)155 (3)
N31—H31A···O3i0.95 (3)1.87 (1)2.795 (3)162 (3)
N31—H31B···O510.96 (1)1.82 (1)2.768 (3)170 (3)
N31—H31C···O10.95 (3)1.92 (1)2.843 (2)165 (3)
O41—H41···O41.00 (4)1.82 (2)2.767 (3)158 (5)
O51—H51···O40.99 (3)1.82 (2)2.757 (3)158 (3)
O61—H61A···O3i0.94 (3)1.81 (3)2.750 (2)172 (4)
O61—H61B···O10.944 (12)1.80 (2)2.687 (2)156 (4)
Symmetry codes: (i) x, y1, z; (ii) x+1, y1/2, z+1.
Selected geometric parameters (Å, º) for (II) top
O1—C11.259 (2)O7—C31.446 (2)
O2—C11.237 (2)C1—C21.545 (2)
O3—C41.253 (2)C2—C31.516 (2)
O4—C41.249 (2)C3—C41.545 (2)
O5—C21.438 (2)
C5—O5—C2—C3156.6 (1)C2—O5—C5—C6179.4 (1)
C13—O7—C3—C2151.0 (1)C3—O7—C13—C14173.4 (1)
O5—C2—C3—O776.5 (1)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N21—H21A···O41i0.96 (1)1.93 (1)2.875 (2)169 (2)
N21—H21B···O40.95 (1)2.02 (1)2.888 (2)150 (2)
N21—H21C···O1ii0.96 (1)1.72 (1)2.673 (2)172 (2)
N31—H31A···O3i0.95 (1)1.87 (1)2.803 (2)168 (2)
N31—H31B···O510.95 (1)1.93 (1)2.807 (2)153 (2)
N31—H31C···O40.96 (1)1.79 (1)2.729 (2)168 (2)
O41—H41A···O30.94 (1)1.88 (1)2.785 (2)160 (2)
O41—H41B···O2ii0.94 (3)2.00 (3)2.931 (2)173 (3)
O51—H51A···O1i0.94 (1)1.86 (1)2.783 (2)168 (2)
O51—H51B···O20.94 (1)1.90 (1)2.804 (2)162 (2)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1/2, z+1/2.
 

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